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Enantioselective, NHC‐Catalyzed Annulations of Trisubstituted Enals and Cyclic N ‐Sulfonylimines via α,β‐Unsaturated Acyl Azoliums
Author(s) -
Kravina Alberto G.,
Mahatthananchai Jessada,
Bode Jeffrey W.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201204145
Subject(s) - enantioselective synthesis , enamine , chemistry , tautomer , nucleophile , catalysis , annulation , imine , organocatalysis , organic chemistry , combinatorial chemistry
All aboard please! A new reaction of enals and cyclic sulfonylimines, as the nucleophiles(!), is the first highly enantioselective NHC‐catalyzed annulation of trisubstituted enals. The catalytically generated α,β‐unsaturated acyl azolium undergoes a reaction with the enamine tautomer of the imine via an aza‐Claisen rearrangement as the key CC bond‐forming step. High yields and enantioselectivities were achieved using β ‐ , α,β‐, and β,β′‐substituted enals.